Senior / Principal Product Designer

Outpost is building the backbone of freight. We’re reinventing how supply chain infrastructure works in America with carrier agnostic truck terminals. As a vertically integrated real estate, operations, and technology company, we acquire and operate mission-critical real estate across the country to serve the largest logistics providers in the world. Backed by $1B from Greenpoint Partners, we’re scaling and building the most valuable logistics network in the country.

We thrive on accountability, integrity, and a shared drive to raise the bar. If you’re excited to reshape the industry alongside a high-performance team with a championship mindset that executes relentlessly, welcome aboard.

We are hiring a Senior or Principal Product Designer to join our Product & Technology team in Seattle. Reporting to our Chief Product & Technology Officer, you will work closely with product, engineering, marketing, and cross-functional stakeholders across Operations and Solutions Engineering to build and extend our design system, delivering polished, user-centered experiences across web, mobile, and drive-up kiosks. The level will be determined based on your experience, scope of ownership, and demonstrated impact.

This is a hands-on role for a designer who thrives working on complex, operationally-critical, multiplayer products and can move very quickly without sacrificing quality. Our users are drivers, guards, yard operators, remote ops, VPs of operations, and IT managers at major logistics companies — people working in loud, fast, physical environments where a confusing, inefficient, or oversimplified interface costs real time at a real gate (potentially even backing up traffic into a highway).

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  Embrace AI as a core part of the design workflow — across research synthesis, prototyping, documentation, and ideation — and actively look for new ways it can raise the quality and speed of design work across the team.

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  Execute high-quality product design work across web, kiosk, and mobile platforms.

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  Translate complex logistics and freight data into clear, intuitive, and actionable interfaces.

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  Contribute to and maintain design system components and patterns in Figma, Lovable, and design-built prototyping tools.

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  Partner with the Product & Technology team to deliver designs that are technically feasible and user-validated.

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  Conduct and synthesize user research using Dovetail to inform design decisions.

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  Design data visualizations and dashboards that surface meaningful insights for internal and external users.

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  Participate in design reviews and contribute structured, high-signal feedback.

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  Stay current on AI interaction paradigms and SaaS UX trends and bring relevant ideas to the team.

• 5–7 years of product design experience.

• Has shipped end-to-end product surfaces and can operate independently on a defined problem area.

• Contributes components and patterns to an existing design system.

• 5-10 years of product design experience, including senior or staff-level scope at a product-led company.

• Has owned a design system end to end — established the architecture, documentation, and adoption model, not just contributed components.

• Sets design direction across multiple product surfaces and influences roadmap and product strategy, not just execution.

• Track record of raising the design bar across a team — mentoring, critique culture, hiring, or establishing practice standards.

• Has designed for at least one domain with hardware, field, or operational constraints (industrial, IoT, logistics, healthcare, fintech ops, or similar).

• Lead role - own design for the entire product, end to end, top to bottom.

• Strong focus on interaction design and data-heavy SaaS applications.

• Proven ability to work within systems and contribute to a shared design library, rather than designing individual screens in isolation.

• Experience designing complex workflows, multi-step processes, and data-rich interfaces.

• Demonstrated willingness to adopt and integrate AI tools into daily design practice.

• Strong communication and collaboration skills across distributed teams — Outpost's Product & Technology team spans Seattle (PT), Austin (CT), and LatAm.

• Proficiency with Figma, Lovable, Dovetail, PostHog, ClickUp, Claude, and /or other AI tools.

• Comfort with logistics, freight, IoT, or similarly technical domains is a plus.

• AI is a native part of the design workflow. Design is actively using Claude for research synthesis, UX copy, and spec writing, and Lovable for rapid prototyping and concept validation — measurably shortening the distance between idea and artifact.

• Designs simultaneously specify the experience and establish reusable patterns and tenets. Outpost's design system is measurably stronger: components are documented, reusable, and actively used by engineering without requiring designer intervention on every implementation.

• Faster cycle time between customer/user feedback → design → spec → engineering, with fewer revision loops due to clearer, higher-fidelity handoff artifacts.

• Every major product surface has a consistent, validated UX that reflects Outpost's design principles and passes internal usability benchmarks.

• Product and design are aligned on priorities, speak the same language in customer-facing conversations, and co-own the quality of what ships.

• Dovetail is populated with synthesized findings from driver, guard, and operator interviews that actively inform roadmap decisions.

• PostHog and product analytics are part of the design workflow, so decisions are grounded in behavioral data, not just intuition.